(5-Amino-1H-imidazol-4-yl)-piperidin-1-yl-methanone | 106232-27-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (5-Amino-1H-imidazol-4-yl)-piperidin-1-yl-methanone
• 英文别名: (4-amino-1H-imidazol-5-yl)-piperidin-1-ylmethanone
• CAS: 106232-27-3
• 化学式: C₉H₁₄N₄O
• 分子量: 194.236
• InChiKey: LGNPFKQORXEBFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  75
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5-Amino-1H-imidazol-4-yl)-piperidin-1-yl-methanone 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 5-diazoimidazole-4-carboxy piperidide
  参考文献：
  名称：

  新型唑并[5,1-d][1,2,3,5]tetrazin-4-ones-抗肿瘤剂替莫唑胺类似​​物的合成

  摘要：

  研究了 5-重氮咪唑和 5-重氮吡唑在与烷基和芳基异氰酸酯反应中的反应性。合成了许多新的咪唑并吡唑并[5,1-d][1,2,3,5]tetrazin-4，它们是替莫唑胺的类似物。结果表明，在类似条件下，重氮唑不与异硫氰酸酯反应。

  DOI：

  10.1007/s11172-016-1522-9
• 作为产物：
  描述：

  4-nitro-5-(piperidinocarbonyl)imidazole 在 palladium on activated charcoal sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (5-Amino-1H-imidazol-4-yl)-piperidin-1-yl-methanone
  参考文献：
  名称：

  Varoli; Burnelli; Garuti, Pharmazie, 1997, vol. 52, # 8, p. 578 - 581

  摘要：

  DOI：

文献信息

• Antitumor imidazotetrazines. 14. Synthesis and antitumor activity of 6- and 8-substituted imidazo[5,1-d]-1,2,3,5-tetrazinones and 8-substituted pyrazolo[5,1-d]-1,2,3,5-tetrazinones
  作者：Edward Lunt、Christopher G. Newton、Christopher Smith、Graham P. Stevens、Malcolm F. G. Stevens、Colin G. Straw、Roger J. A. Walsh、Peter J. Warren、Christian Fizames

  DOI：10.1021/jm00385a018

  日期：1987.2

  The systematic variation of the potent antitumor agent mitozolomide (1) is extended to cover alteration of substituents at positions 6 and 8 and to change the imidazo[5,1-d]-1,2,3,5-tetrazinone (1) skeleton to the isomeric pyrazolo-[5,1-d]-1,2,3,5-tetrazinone (17) skeleton. The series of eight 6-alkyl and 6-aralkyl derivatives of 1 showed optimal antitumor activity when the group was small or linear, but activity diminished as size and branching of this substituent increased. This may reflect altered transport characteristics, or failure of the enlarged derivatives to fit a binding site, or possibly a reduced tendency for the derivatives having bulky groups at position 6 to hydrolytically generate the putatively active triazenes (21). Testing of 14 derivatives of 1 differently substituted at position 8 revealed a complex structure-activity relationship, with good antitumor activity obtained for carbamoyl and sulfamoyl groups bearing small substituents. The 8-methylsulfonyl compound had noteworthy activity, but the 8-cyano, 8-nitro, and 8-phenyl derivatives were devoid of useful antitumor activity in these tests. From the limited number of pyrazolotetrazinones (17) reported here, it is suggested that the same conclusions as regards activity also hold true for this ring system.
• ——
  作者：E. V. Sadchikova、V. S. Mokrushin

  DOI：10.1023/a:1025605512301

  日期：——

  Diazotization of 4-R-5-aminoimidazoles (R = CONHAr, CONHAlk, morphohnocarbonyl, or piperidinocarbonyl) with sodium nitrite in aqueous solutions of mineral acids afforded the corresponding 5-diazoimidazoles, whereas the reactions in concentrated tetrafluoroboric acid produced imidazolyl-5-diazonium salts. In the solid phase, diazonium salts are transformed into the corresponding diazo compounds.
• Synthesis and structure of new imidazo- and pyrazolo[5,1-d][1,2,3,5]thiatriazines based on the reaction of diazoazoles with acyl isothiocyanates controlled by S⋯O interaction
  作者：Elena V. Sadchikova、Vasiliy A. Bakulev、Julia O. Subbotina、Darya L. Privalova、Wim Dehaen、Kristof Van Hecke、Koen Robeyns、Luc Van Meervelt、Vladimir S. Mokrushin

  DOI：10.1016/j.tet.2013.06.062

  日期：2013.8

  5-Diazoimidazoles and 5-diazopyrazoles have been shown to react with acyl isothiocyanates yielding the imidazo- and pyrazolo[5,1-d][1,2,3,5]thiatriazines stabilized by a nonbonded S center dot center dot center dot O interaction. In contrast to acyl isothiocyanates, alkyl-, aryl-, and arylsulfonyl isothiocyanates do not react with 5-diazoazoles. The nature and the strength of stabilizing intramolecular interaction between non-bonded S and O atoms have been studied by X-ray analysis for mono crystals and DFT calculations for selected azolo[5,1-d] [1,2,3,5]thiatriazines. The interaction was described in terms of Weinhold covalence ratio factors, NBO, and AIM schemes. The reaction discovered was used to develop an efficient approach toward the new 8-substituted 4-ethoxycarbonylimino-4-benzoyl- and 4-(3,4,5,6-tetrafluorobenzoy)iminoimidazo(pyrazolo)[5,1-d][1,2,3,5]thiatriazines. (C) 2013 Elsevier Ltd. All rights reserved.